Coenzym Q-10

Coenzyme Q10 Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

• Beschreibung

  Coenzyme Q₁₀ (CoQ₁₀) is a quinone that is found throughout the human body in cell membranes, primarily in mitochondrial membranes, with the highest levels in the heart, lungs, liver, kidneys, spleen, pancreas, and adrenal glands. It exists in three redox states: fully oxidized (CoQ₁₀/ubiquinone), partially reduced (semiquinone or ubisemiquinone), and fully reduced (ubiquinol; ). CoQ₁₀ acts as an electron shuttle in the electron transport chain via its reduction to ubiquinol between mitochondrial complexes I and II, also known as NADH dehydrogenase and succinate dehydrogenase, respectively, and mitochondrial complex III, also known as cytochrome bc₁ complex. CoQ₁₀ is also reduced to ubiquinol by ferroptosis suppressor protein 1 (FSP1) with NADPH as a cofactor, and ubiquinol traps lipid peroxyl radicals and inhibits lipid peroxidation helping to prevent ferroptosis. Mutations in genes encoding enzymes involved in CoQ₁₀ biosynthesis lead to primary CoQ₁₀ deficiency, which is characterized by encephalopathy, cerebellar ataxia, infantile multisystemic form, nephropathy, and isolated myopathy. Secondary CoQ₁₀ deficiency, induced by non-genetic impaired CoQ₁₀ biosynthesis, insufficient CoQ₁₀ intake, or excessive CoQ₁₀ utilization, has been observed in a variety of conditions, including ataxia-oculomotor-apraxia 1 (AOA1), mitochondrial diseases, and hypercholesteremia with statin therapy. Formulations containing CoQ₁₀ have been used in the treatment of CoQ₁₀ deficiency.

• Chemische Eigenschaften

  Yellow-Orange Crystalline Powder

• Originator

  Neuquinon,Eisai,Japan,1974

• Occurrence

  Coenzyme Q10 is found in dietary sources. Coenzyme Qmolecules have side chains of differentlengths in different types of organismsbut function in similar ways.

• Verwenden

  Coenzyme Q10 (CoQ10) is a naturally occurring quinone found throughout the body in cell membranes, primarily in mitochondrial membranes, with highest concentrations in the heart, lungs, liver, kidneys, spleen, pancreas, and adrenal glands. It is a component of the electron transport chain and participates in aerobic cellular respiration, generating energy in the form of ATP. In its reduced form, CoQ10 acts as an antioxidant, preventing the formation of reactive oxygen species. CoQ10 deficiencies have been associated with heart failure, hypertension, parkinsonism, mitochondrial encephalomyopathies, and other chronic diseases.[Cayman Chemical]

• Verwenden

  Ubidecarenone is also known as coenzyme Q10 it is a powerful antioxidant that is naturally found in the cells. It acts as a free radical neutraliser.

• Definition

  ChEBI: Coenzyme Q10 is a ubiquinone having a side chain of 10 isoprenoid units. In the naturally occurring isomer, all isoprenyl double bonds are in the E- configuration. It has a role as a human metabolite, a ferroptosis inhibitor and an antioxidant. It is found in animal organs and yeast with active in the citric acid cycle in carbohydrate metabolism.

• Manufacturing Process

  A small fermentation tank (5,000 parts by volume capacity) was charged with 3,000 parts by volume of a culture medium (pH 6.0) comprising 3% glucose, 1% polypepton, 0.5% yeast extract and 0.5% malt extract. The medium was sterilized by heating in a conventional manner and cooled. This medium was inoculated with 150 parts by volume of a pre-culture of Sporidiobolus ruinenii CBS-5001, which had been prepared by growing the same strain on a medium of the same composition as above at 28°C for one day. The inoculated medium was incubated at 28°C and under agitation at 800 rpm with sparging at a rate of 3,000 parts by volume per minute for 24 hours. During this fermentation period, the medium was maintained at pH 6.0 with ammonia and sulfuric acid.
  The resultant fermentation broth was centrifuged to harvest the microbial cells, and they were washed with water and centrifuged a second time, whereupon a living cell paste was obtained. (There was obtained an amount of cells equivalent to 54 parts on a dry basis, which contained 920 μg of ubiquinone-10 per gram of dry cells.)
  The moist cells were suspended in 750 parts of volume of ethanol and extracted by warming at 60°C for 1 hour. A total of 3 extractions were carried out in a similar manner and the extracts were pooled, diluted with water and further extracted three times with 1,000 parts of volume portions of n_x0002_hexane. The n-hexane layer was concentrated to dryness under reduced pressure to recover 4.12 parts of a yellow oil. This oily residue was dissolved in 6 parts by volume of benzene and passed through a column (500 parts by volume capacity) packed with Floridil (100 to 200 meshes). Elution was carried out using benzene and the eluate was collected in 10 parts by volume fractions. Each fraction was analyzed by thin-layer chromatography and color reaction and the fractions rich in ubiquinone-10 were pooled and concentrated under reduced pressure. By this procedure was obtained 0.562 part of a yellow oil. This product was dissolved in 5 parts by volume of chloroform, coated onto a thin layer plate of silica gel GF254 (silica gel with calcium sulfate) and developed with benzene. The fractions corresponding to ubiquinone-10 were extracted, whereby 0.054 part of a yellow oil was obtained. This oil was dissolved in 10 parts by volume of ethanol and allowed to cool, whereupon 0.029 part of yellow crystals of ubiquinone-10 were obtained, its melting point 48° to 50°C.
  There are also synthetic routes to the ubiquinones as described in US Patents 3,068,295; 3,896,153 and 4,062,879.

• Therapeutic Function

  UBIDECARENONE

• Allgemeine Beschreibung

  Ubidecarenone, referred to as coenzyme Q, is abundantly available in human cells, with major proportions being present in vital body organs such as heart and kidneys. It plays an important role in cell metabolism owing to its significant contribution to the electron transport pathway. It is a strong antioxidant and acts as an essential enzyme catalyst in mitochondrial oxidative phosphorylation.

• Biologische Aktivität

  Component of the mitochondrial transporter chain that behaves as a powerful antioxidant. Displays neuroprotective activity.

• Biochem/physiol Actions

  Coenzyme Q10 is an endogenous cellular antioxidant and an essential component of the electron transfer chain. CoQ10 takes part in aerobic cellular respiration and generation of energy in the form of ATP.

• Nebenwirkungen

  Mild side effects might include digestive problems such as: Upper abdominal pain; Loss of appetite; Nausea and vomiting; Diarrhea.
  Other possible side effects may include: Headaches and dizziness; Insomnia; Fatigue; Skin itching or rashes; Irritability or agitation.

• Arzneimittelwechselwirkung

  Coenzyme Q10 supplements may interact with some antihypertensive (those that lower blood pressure) and chemotherapy drugs. Coenzyme Q10 may increase the risk of blood clots in people who take the anticoagulant warfarin by decreasing warfarin's effectiveness.

• läuterung methode

  Purify it by recrystallisation from EtOH, EtOH/Me2CO or Et2O/EtOH and by chromatography on silica gel using isoPrOH/Et2O (3:1) to give orange crystals. It has max 270nm ( 15,170) in pet ether. [Terao et al. J Org Chem 44 868 1979, NMR and MS: Naruta et al. J Org Chem 45 4097 1980, IR: Lester et al. Biochem Biophys Acta 42 1278 1959, NMR: Planta et al. Helv Chim Acta 42 1278 1959; Morton Biochemical Spectroscopy (Adam Hilger, London, 1975) p 491].

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